6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-2-O-methoxymethyl-5-thio-D-glucopyranose (S)-S-oxide

Base Information

Chemical Name:6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-2-O-methoxymethyl-5-thio-D-glucopyranose (S)-S-oxide
CAS No.:592517-60-7
Molecular Formula:C₁₈H₂₄O₇S
Molecular Weight:384.45
Hs Code.:

Synonyms:6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-2-O-methoxymethyl-5-thio-D-glucopyranose (S)-S-oxide

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Chemical Property of 6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-2-O-methoxymethyl-5-thio-D-glucopyranose (S)-S-oxide

Chemical Property:

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Technology Process of 6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-2-O-methoxymethyl-5-thio-D-glucopyranose (S)-S-oxide

There total 4 articles about 6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-2-O-methoxymethyl-5-thio-D-glucopyranose (S)-S-oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 44.0%

: 592517-52-7
6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-2-O-methoxymethyl-5-thio-D-glucopyranose

: 592517-56-1
6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-2-O-methoxymethyl-5-thio-D-glucopyranose (R)-S-oxide

: 592517-60-7
6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-2-O-methoxymethyl-5-thio-D-glucopyranose (S)-S-oxide

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -20 ℃; for 0.5h;
DOI:10.1016/j.tet.2004.06.006

Reference yield:

: 592517-48-1
6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-5-thio-D-glucopyranose

: 592517-60-7
6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-2-O-methoxymethyl-5-thio-D-glucopyranose (S)-S-oxide

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / 20 °C

2: 43 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / -20 °C

With N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1016/j.tet.2004.06.006

Reference yield:

: 65-85-0,8013-63-6
benzoic acid

: 592517-60-7
6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-2-O-methoxymethyl-5-thio-D-glucopyranose (S)-S-oxide

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / PPh₃; DEAD / tetrahydrofuran / 20 °C

2: 60 percent / (i-Pr)2NEt / CH₂Cl₂ / 0 °C

3: mCPBA / CH₂Cl₂ / -20 °C

With N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 1: Mitsunobu reaction;
DOI:10.1016/S0040-4039(03)00842-6